# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Dr pengfei wang'
_publ_contact_author_email       wangpf@mail.ipc.ac.cn

_publ_section_title              
;
Aggregation-induced emission enhancement
materials with large red shifts and their
self-assembled crystal microstructures
;
loop_
_publ_author_name
'Pengfei Wang'
'Qing Dai'
'Weimin Liu'
'Lintao Zeng'
'Chun-sing Lee'
'Jiasheng Wu'

# Attachment 'BzBMN.cif'

data_a
_database_code_depnum_ccdc_archive 'CCDC 806623'
#TrackingRef 'BzBMN.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N3 O'
_chemical_formula_sum            'C21 H21 N3 O'
_chemical_formula_weight         331.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.797(3)
_cell_length_b                   17.007(3)
_cell_length_c                   8.2934(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.80(3)
_cell_angle_gamma                90.00
_cell_volume                     1788.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    867
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9543
_exptl_absorpt_correction_T_max  0.9734
_exptl_absorpt_process_details   'ABSCOR by T.Higashi 8 March, 1995'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6022
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3149
_reflns_number_gt                2738
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.4869P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3149
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1180
_refine_ls_goodness_of_fit_ref   1.254
_refine_ls_restrained_S_all      1.254
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.39738(10) 0.04622(8) 0.27587(17) 0.0291(4) Uani 1 1 d . . .
N1 N 0.77520(12) 0.01948(10) 0.3128(2) 0.0263(4) Uani 1 1 d . . .
N2 N 0.42744(16) -0.26084(13) -0.0971(3) 0.0548(6) Uani 1 1 d . . .
N3 N 0.12173(15) -0.17827(12) 0.0002(3) 0.0446(5) Uani 1 1 d . . .
C1 C 0.90477(17) -0.03123(15) 0.1391(3) 0.0384(6) Uani 1 1 d . . .
H1A H 0.9660 -0.0660 0.1415 0.058 Uiso 1 1 calc R . .
H1B H 0.9246 0.0223 0.1117 0.058 Uiso 1 1 calc R . .
H1C H 0.8479 -0.0500 0.0570 0.058 Uiso 1 1 calc R . .
C2 C 0.86713(15) -0.03111(13) 0.3051(3) 0.0306(5) Uani 1 1 d . . .
H2A H 0.8490 -0.0856 0.3331 0.037 Uiso 1 1 calc R . .
H2B H 0.9255 -0.0132 0.3876 0.037 Uiso 1 1 calc R . .
C3 C 0.80698(19) 0.10248(15) 0.5616(3) 0.0406(6) Uani 1 1 d . . .
H3A H 0.8215 0.1568 0.5974 0.061 Uiso 1 1 calc R . .
H3B H 0.8648 0.0684 0.6092 0.061 Uiso 1 1 calc R . .
H3C H 0.7409 0.0848 0.5972 0.061 Uiso 1 1 calc R . .
C4 C 0.79727(15) 0.09854(12) 0.3775(2) 0.0277(5) Uani 1 1 d . . .
H4A H 0.7400 0.1342 0.3306 0.033 Uiso 1 1 calc R . .
H4B H 0.8638 0.1175 0.3426 0.033 Uiso 1 1 calc R . .
C5 C 0.67564(14) -0.00758(12) 0.2681(2) 0.0234(4) Uani 1 1 d . . .
C6 C 0.58630(14) 0.03607(12) 0.2985(2) 0.0235(4) Uani 1 1 d . . .
H6A H 0.5953 0.0849 0.3542 0.028 Uiso 1 1 calc R . .
C7 C 0.48641(14) 0.00798(12) 0.2477(2) 0.0225(4) Uani 1 1 d . . .
C8 C 0.46814(15) -0.06456(11) 0.1640(2) 0.0228(4) Uani 1 1 d . . .
C9 C 0.55868(15) -0.10775(12) 0.1403(2) 0.0272(5) Uani 1 1 d . . .
H9A H 0.5498 -0.1573 0.0871 0.033 Uiso 1 1 calc R . .
C10 C 0.65839(15) -0.08154(12) 0.1902(3) 0.0279(5) Uani 1 1 d . . .
H10A H 0.7170 -0.1132 0.1726 0.033 Uiso 1 1 calc R . .
C11 C 0.40564(15) 0.11715(11) 0.3683(2) 0.0249(5) Uani 1 1 d . . .
H11A H 0.4449 0.1572 0.3142 0.030 Uiso 1 1 calc R . .
H11B H 0.4440 0.1073 0.4784 0.030 Uiso 1 1 calc R . .
C12 C 0.29546(15) 0.14578(11) 0.3804(2) 0.0225(4) Uani 1 1 d . . .
C13 C 0.28264(17) 0.21187(13) 0.4735(3) 0.0346(5) Uani 1 1 d . . .
H13A H 0.3427 0.2368 0.5319 0.041 Uiso 1 1 calc R . .
C14 C 0.18296(19) 0.24181(14) 0.4821(3) 0.0435(6) Uani 1 1 d . . .
H14A H 0.1751 0.2874 0.5455 0.052 Uiso 1 1 calc R . .
C15 C 0.09511(18) 0.20597(14) 0.3992(3) 0.0404(6) Uani 1 1 d . . .
H15A H 0.0268 0.2269 0.4046 0.048 Uiso 1 1 calc R . .
C16 C 0.10711(17) 0.13983(14) 0.3089(3) 0.0363(5) Uani 1 1 d . . .
H16A H 0.0467 0.1147 0.2520 0.044 Uiso 1 1 calc R . .
C17 C 0.20637(15) 0.10938(12) 0.2998(2) 0.0280(5) Uani 1 1 d . . .
H17A H 0.2136 0.0632 0.2379 0.034 Uiso 1 1 calc R . .
C18 C 0.36295(15) -0.08980(11) 0.1165(2) 0.0227(4) Uani 1 1 d . . .
H18A H 0.3110 -0.0550 0.1472 0.027 Uiso 1 1 calc R . .
C19 C 0.32281(15) -0.15504(12) 0.0347(2) 0.0241(4) Uani 1 1 d . . .
C20 C 0.38225(16) -0.21391(13) -0.0353(3) 0.0318(5) Uani 1 1 d . . .
C21 C 0.21130(16) -0.16812(12) 0.0149(2) 0.0279(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0188(7) 0.0285(8) 0.0398(9) -0.0130(7) 0.0030(6) 0.0020(6)
N1 0.0186(8) 0.0332(10) 0.0268(9) -0.0037(8) 0.0022(7) -0.0011(7)
N2 0.0404(12) 0.0479(14) 0.0707(16) -0.0291(12) -0.0122(11) 0.0115(10)
N3 0.0305(11) 0.0479(13) 0.0552(14) -0.0026(10) 0.0052(9) -0.0128(9)
C1 0.0293(11) 0.0471(15) 0.0408(13) -0.0045(11) 0.0127(10) 0.0003(10)
C2 0.0185(10) 0.0410(13) 0.0311(11) -0.0027(10) -0.0003(8) 0.0017(9)
C3 0.0498(14) 0.0412(14) 0.0301(12) -0.0041(11) 0.0025(10) -0.0001(11)
C4 0.0219(10) 0.0305(12) 0.0306(11) 0.0027(9) 0.0032(8) -0.0048(9)
C5 0.0224(10) 0.0276(11) 0.0203(10) 0.0023(8) 0.0030(8) -0.0012(8)
C6 0.0247(10) 0.0234(10) 0.0226(10) -0.0023(8) 0.0042(8) -0.0008(8)
C7 0.0195(9) 0.0265(11) 0.0222(10) 0.0008(8) 0.0048(8) 0.0032(8)
C8 0.0220(9) 0.0243(11) 0.0220(10) 0.0022(8) 0.0032(8) -0.0006(8)
C9 0.0279(11) 0.0239(11) 0.0304(11) -0.0050(9) 0.0057(9) -0.0003(9)
C10 0.0196(10) 0.0304(12) 0.0343(12) -0.0025(9) 0.0061(8) 0.0036(9)
C11 0.0236(10) 0.0223(11) 0.0283(11) -0.0045(9) 0.0019(8) -0.0011(8)
C12 0.0264(10) 0.0209(10) 0.0209(10) 0.0027(8) 0.0056(8) 0.0008(8)
C13 0.0360(12) 0.0289(12) 0.0407(13) -0.0101(10) 0.0120(10) -0.0056(10)
C14 0.0498(14) 0.0275(12) 0.0588(16) -0.0100(11) 0.0273(12) 0.0030(11)
C15 0.0299(12) 0.0385(14) 0.0567(16) 0.0044(12) 0.0198(11) 0.0103(11)
C16 0.0262(11) 0.0435(14) 0.0398(13) 0.0021(11) 0.0064(9) 0.0025(10)
C17 0.0259(11) 0.0285(12) 0.0299(11) -0.0035(9) 0.0054(9) 0.0027(9)
C18 0.0239(10) 0.0234(10) 0.0213(10) 0.0020(8) 0.0049(8) 0.0027(8)
C19 0.0231(10) 0.0241(11) 0.0244(10) 0.0036(9) 0.0008(8) 0.0009(8)
C20 0.0256(11) 0.0296(12) 0.0370(13) -0.0070(10) -0.0072(9) -0.0008(10)
C21 0.0303(12) 0.0246(11) 0.0283(12) 0.0000(9) 0.0024(9) -0.0048(9)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.359(2) . ?
O1 C11 1.425(2) . ?
N1 C5 1.358(2) . ?
N1 C4 1.461(3) . ?
N1 C2 1.466(2) . ?
N2 C20 1.146(3) . ?
N3 C21 1.149(3) . ?
C1 C2 1.519(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.516(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.414(3) . ?
C5 C10 1.418(3) . ?
C6 C7 1.376(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.419(3) . ?
C8 C9 1.408(3) . ?
C8 C18 1.417(3) . ?
C9 C10 1.362(3) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.508(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.386(3) . ?
C12 C17 1.387(3) . ?
C13 C14 1.384(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.378(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.372(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.383(3) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 C19 1.364(3) . ?
C18 H18A 0.9500 . ?
C19 C20 1.427(3) . ?
C19 C21 1.431(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C11 119.63(15) . . ?
C5 N1 C4 122.65(16) . . ?
C5 N1 C2 121.20(17) . . ?
C4 N1 C2 116.09(15) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C1 113.26(18) . . ?
N1 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
N1 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C3 113.34(17) . . ?
N1 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
N1 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
N1 C5 C6 121.64(18) . . ?
N1 C5 C10 120.49(18) . . ?
C6 C5 C10 117.86(17) . . ?
C7 C6 C5 120.20(19) . . ?
C7 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
O1 C7 C6 123.15(18) . . ?
O1 C7 C8 114.43(16) . . ?
C6 C7 C8 122.41(18) . . ?
C9 C8 C18 124.87(18) . . ?
C9 C8 C7 115.97(17) . . ?
C18 C8 C7 119.12(17) . . ?
C10 C9 C8 122.78(19) . . ?
C10 C9 H9A 118.6 . . ?
C8 C9 H9A 118.6 . . ?
C9 C10 C5 120.70(19) . . ?
C9 C10 H10A 119.7 . . ?
C5 C10 H10A 119.7 . . ?
O1 C11 C12 107.89(15) . . ?
O1 C11 H11A 110.1 . . ?
C12 C11 H11A 110.1 . . ?
O1 C11 H11B 110.1 . . ?
C12 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
C13 C12 C17 118.60(19) . . ?
C13 C12 C11 118.77(18) . . ?
C17 C12 C11 122.61(18) . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C16 C15 C14 119.4(2) . . ?
C16 C15 H15A 120.3 . . ?
C14 C15 H15A 120.3 . . ?
C15 C16 C17 120.6(2) . . ?
C15 C16 H16A 119.7 . . ?
C17 C16 H16A 119.7 . . ?
C16 C17 C12 120.5(2) . . ?
C16 C17 H17A 119.7 . . ?
C12 C17 H17A 119.7 . . ?
C19 C18 C8 131.62(19) . . ?
C19 C18 H18A 114.2 . . ?
C8 C18 H18A 114.2 . . ?
C18 C19 C20 125.97(18) . . ?
C18 C19 C21 119.06(18) . . ?
C20 C19 C21 114.97(18) . . ?
N2 C20 C19 177.4(2) . . ?
N3 C21 C19 179.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C1 86.3(2) . . . . ?
C4 N1 C2 C1 -96.4(2) . . . . ?
C5 N1 C4 C3 91.6(2) . . . . ?
C2 N1 C4 C3 -85.7(2) . . . . ?
C4 N1 C5 C6 -7.2(3) . . . . ?
C2 N1 C5 C6 169.95(18) . . . . ?
C4 N1 C5 C10 173.34(18) . . . . ?
C2 N1 C5 C10 -9.5(3) . . . . ?
N1 C5 C6 C7 178.21(18) . . . . ?
C10 C5 C6 C7 -2.4(3) . . . . ?
C11 O1 C7 C6 -2.9(3) . . . . ?
C11 O1 C7 C8 175.89(16) . . . . ?
C5 C6 C7 O1 178.67(18) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
O1 C7 C8 C9 -176.82(17) . . . . ?
C6 C7 C8 C9 2.0(3) . . . . ?
O1 C7 C8 C18 0.8(3) . . . . ?
C6 C7 C8 C18 179.60(18) . . . . ?
C18 C8 C9 C10 -179.03(19) . . . . ?
C7 C8 C9 C10 -1.6(3) . . . . ?
C8 C9 C10 C5 -0.8(3) . . . . ?
N1 C5 C10 C9 -177.78(19) . . . . ?
C6 C5 C10 C9 2.8(3) . . . . ?
C7 O1 C11 C12 -179.69(16) . . . . ?
O1 C11 C12 C13 176.15(18) . . . . ?
O1 C11 C12 C17 -4.9(3) . . . . ?
C17 C12 C13 C14 -1.7(3) . . . . ?
C11 C12 C13 C14 177.3(2) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C13 C14 C15 C16 0.5(4) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C15 C16 C17 C12 -0.8(3) . . . . ?
C13 C12 C17 C16 1.8(3) . . . . ?
C11 C12 C17 C16 -177.16(19) . . . . ?
C9 C8 C18 C19 -3.5(3) . . . . ?
C7 C8 C18 C19 179.1(2) . . . . ?
C8 C18 C19 C20 -4.7(4) . . . . ?
C8 C18 C19 C21 175.1(2) . . . . ?
C18 C19 C20 N2 -128(6) . . . . ?
C21 C19 C20 N2 52(6) . . . . ?
C18 C19 C21 N3 -29(27) . . . . ?
C20 C19 C21 N3 151(27) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.043

# Attachment 'BzFAN.cif'

data_b
_database_code_depnum_ccdc_archive 'CCDC 806624'
#TrackingRef 'BzFAN.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H22 N2 O2'
_chemical_formula_sum            'C21 H22 N2 O2'
_chemical_formula_weight         334.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.3916(19)
_cell_length_b                   11.835(2)
_cell_length_c                   16.208(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.66(3)
_cell_angle_gamma                90.00
_cell_volume                     1792.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    879
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.61
_exptl_crystal_size_min          0.51
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9527
_exptl_absorpt_correction_T_max  0.9602
_exptl_absorpt_process_details   'ABSCOR by T.Higashi 8 March, 1995'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6355
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3330
_reflns_number_gt                2806
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.3604P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3330
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.0989
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.26400(12) 0.10507(8) 0.05065(6) 0.0368(3) Uani 1 1 d . . .
O2 O -0.15073(13) 0.31219(11) -0.20664(7) 0.0523(3) Uani 1 1 d . . .
N1 N 0.33634(13) -0.29363(10) 0.01042(7) 0.0331(3) Uani 1 1 d . . .
N2 N -0.14601(16) 0.02746(14) -0.26209(9) 0.0522(4) Uani 1 1 d . . .
C1 C 0.27696(15) -0.19347(12) -0.01417(9) 0.0291(3) Uani 1 1 d . . .
C2 C 0.30689(15) -0.09347(12) 0.03205(9) 0.0295(3) Uani 1 1 d . . .
H2A H 0.3726 -0.0957 0.0805 0.035 Uiso 1 1 calc R . .
C3 C 0.24206(15) 0.00687(12) 0.00775(9) 0.0288(3) Uani 1 1 d . . .
C4 C 0.14514(15) 0.01636(13) -0.06535(9) 0.0295(3) Uani 1 1 d . . .
C5 C 0.12075(16) -0.08407(13) -0.11131(9) 0.0333(3) Uani 1 1 d . . .
H5A H 0.0582 -0.0814 -0.1610 0.040 Uiso 1 1 calc R . .
C6 C 0.18212(16) -0.18420(13) -0.08812(9) 0.0333(3) Uani 1 1 d . . .
H6A H 0.1616 -0.2492 -0.1216 0.040 Uiso 1 1 calc R . .
C7 C 0.30906(17) -0.39709(13) -0.03830(10) 0.0368(4) Uani 1 1 d . . .
H7A H 0.3917 -0.4487 -0.0273 0.044 Uiso 1 1 calc R . .
H7B H 0.3005 -0.3777 -0.0980 0.044 Uiso 1 1 calc R . .
C8 C 0.1743(2) -0.45767(15) -0.01867(11) 0.0481(4) Uani 1 1 d . . .
H8A H 0.1614 -0.5262 -0.0526 0.072 Uiso 1 1 calc R . .
H8B H 0.0917 -0.4078 -0.0309 0.072 Uiso 1 1 calc R . .
H8C H 0.1827 -0.4783 0.0402 0.072 Uiso 1 1 calc R . .
C9 C 0.42554(17) -0.30724(13) 0.08940(9) 0.0348(4) Uani 1 1 d . . .
H9A H 0.4170 -0.3860 0.1089 0.042 Uiso 1 1 calc R . .
H9B H 0.3891 -0.2567 0.1312 0.042 Uiso 1 1 calc R . .
C10 C 0.58232(17) -0.28079(16) 0.08311(11) 0.0463(4) Uani 1 1 d . . .
H10A H 0.6364 -0.2914 0.1374 0.069 Uiso 1 1 calc R . .
H10B H 0.5919 -0.2023 0.0652 0.069 Uiso 1 1 calc R . .
H10C H 0.6198 -0.3315 0.0427 0.069 Uiso 1 1 calc R . .
C11 C 0.36384(16) 0.10752(12) 0.12329(9) 0.0319(3) Uani 1 1 d . . .
H11A H 0.4611 0.0888 0.1088 0.038 Uiso 1 1 calc R . .
H11B H 0.3363 0.0516 0.1643 0.038 Uiso 1 1 calc R . .
C12 C 0.36170(15) 0.22447(12) 0.15876(8) 0.0277(3) Uani 1 1 d . . .
C13 C 0.48775(16) 0.27454(13) 0.19130(9) 0.0324(3) Uani 1 1 d . . .
H13A H 0.5757 0.2351 0.1903 0.039 Uiso 1 1 calc R . .
C14 C 0.48681(18) 0.38170(14) 0.22536(10) 0.0401(4) Uani 1 1 d . . .
H14A H 0.5742 0.4153 0.2476 0.048 Uiso 1 1 calc R . .
C15 C 0.36015(18) 0.44035(14) 0.22741(9) 0.0400(4) Uani 1 1 d . . .
H15A H 0.3600 0.5139 0.2509 0.048 Uiso 1 1 calc R . .
C16 C 0.23417(18) 0.39108(14) 0.19496(10) 0.0416(4) Uani 1 1 d . . .
H16A H 0.1466 0.4310 0.1958 0.050 Uiso 1 1 calc R . .
C17 C 0.23431(17) 0.28373(14) 0.16114(10) 0.0385(4) Uani 1 1 d . . .
H17A H 0.1466 0.2502 0.1394 0.046 Uiso 1 1 calc R . .
C18 C 0.08283(15) 0.12241(13) -0.08690(9) 0.0316(3) Uani 1 1 d . . .
H18A H 0.1161 0.1821 -0.0508 0.038 Uiso 1 1 calc R . .
C19 C -0.01660(15) 0.15554(14) -0.15000(9) 0.0334(4) Uani 1 1 d . . .
C20 C -0.05978(17) 0.27300(15) -0.15616(10) 0.0413(4) Uani 1 1 d . . .
H20A H -0.0127 0.3240 -0.1172 0.050 Uiso 1 1 calc R . .
C21 C -0.08674(16) 0.08226(15) -0.21142(10) 0.0374(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0488(6) 0.0259(6) 0.0320(6) -0.0020(4) -0.0145(5) 0.0011(5)
O2 0.0489(7) 0.0617(8) 0.0451(7) 0.0140(6) -0.0015(6) 0.0189(6)
N1 0.0385(7) 0.0268(7) 0.0329(7) -0.0023(5) -0.0023(5) -0.0026(5)
N2 0.0419(8) 0.0661(11) 0.0450(8) -0.0037(8) -0.0132(7) 0.0000(8)
C1 0.0290(7) 0.0294(8) 0.0289(7) -0.0006(6) 0.0036(6) -0.0044(6)
C2 0.0311(7) 0.0302(8) 0.0260(7) 0.0005(6) -0.0029(6) -0.0043(6)
C3 0.0319(8) 0.0281(8) 0.0258(7) -0.0018(6) -0.0005(6) -0.0052(6)
C4 0.0286(7) 0.0325(8) 0.0268(7) 0.0002(6) -0.0004(6) -0.0023(6)
C5 0.0321(8) 0.0392(9) 0.0269(7) -0.0027(6) -0.0048(6) -0.0026(7)
C6 0.0360(8) 0.0325(9) 0.0302(7) -0.0077(6) -0.0025(6) -0.0041(7)
C7 0.0421(9) 0.0272(8) 0.0407(9) -0.0053(7) 0.0011(7) -0.0007(7)
C8 0.0559(11) 0.0372(10) 0.0513(10) -0.0057(8) 0.0049(8) -0.0140(8)
C9 0.0410(8) 0.0277(8) 0.0343(8) 0.0043(6) -0.0031(6) -0.0015(7)
C10 0.0387(9) 0.0507(11) 0.0484(10) 0.0012(8) -0.0012(8) 0.0011(8)
C11 0.0362(8) 0.0279(8) 0.0289(7) 0.0001(6) -0.0101(6) -0.0012(6)
C12 0.0329(8) 0.0272(8) 0.0222(7) 0.0022(6) -0.0015(6) -0.0024(6)
C13 0.0328(8) 0.0344(8) 0.0290(7) -0.0020(6) -0.0015(6) -0.0007(6)
C14 0.0423(9) 0.0383(9) 0.0386(9) -0.0083(7) -0.0025(7) -0.0098(7)
C15 0.0589(11) 0.0285(9) 0.0330(8) -0.0050(7) 0.0063(7) -0.0029(8)
C16 0.0421(9) 0.0370(9) 0.0464(9) 0.0000(7) 0.0081(7) 0.0080(8)
C17 0.0313(8) 0.0377(9) 0.0452(9) -0.0017(7) -0.0023(7) -0.0040(7)
C18 0.0288(7) 0.0370(9) 0.0288(7) -0.0021(6) 0.0013(6) -0.0022(6)
C19 0.0281(7) 0.0428(9) 0.0290(7) 0.0012(7) 0.0015(6) 0.0013(7)
C20 0.0389(9) 0.0482(10) 0.0365(8) 0.0036(8) 0.0015(7) 0.0075(8)
C21 0.0270(8) 0.0507(10) 0.0334(8) 0.0052(7) -0.0023(6) 0.0047(7)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.3596(17) . ?
O1 C11 1.4312(17) . ?
O2 C20 1.2150(19) . ?
N1 C1 1.3531(19) . ?
N1 C7 1.4658(19) . ?
N1 C9 1.4679(19) . ?
N2 C21 1.147(2) . ?
C1 C2 1.414(2) . ?
C1 C6 1.425(2) . ?
C2 C3 1.374(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.426(2) . ?
C4 C5 1.409(2) . ?
C4 C18 1.414(2) . ?
C5 C6 1.355(2) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.515(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.519(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.500(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.381(2) . ?
C12 C17 1.391(2) . ?
C13 C14 1.384(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.380(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.376(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.384(2) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 C19 1.372(2) . ?
C18 H18A 0.9500 . ?
C19 C21 1.431(2) . ?
C19 C20 1.449(2) . ?
C20 H20A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C11 119.47(11) . . ?
C1 N1 C7 121.87(12) . . ?
C1 N1 C9 122.42(12) . . ?
C7 N1 C9 115.63(12) . . ?
N1 C1 C2 121.50(13) . . ?
N1 C1 C6 121.36(13) . . ?
C2 C1 C6 117.14(13) . . ?
C3 C2 C1 120.80(13) . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 H2A 119.6 . . ?
O1 C3 C2 123.47(12) . . ?
O1 C3 C4 114.19(13) . . ?
C2 C3 C4 122.33(13) . . ?
C5 C4 C18 125.19(13) . . ?
C5 C4 C3 115.47(13) . . ?
C18 C4 C3 119.34(13) . . ?
C6 C5 C4 123.27(13) . . ?
C6 C5 H5A 118.4 . . ?
C4 C5 H5A 118.4 . . ?
C5 C6 C1 120.94(14) . . ?
C5 C6 H6A 119.5 . . ?
C1 C6 H6A 119.5 . . ?
N1 C7 C8 112.78(13) . . ?
N1 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 113.12(13) . . ?
N1 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
N1 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 C12 107.55(11) . . ?
O1 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
O1 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C13 C12 C17 118.71(14) . . ?
C13 C12 C11 119.93(13) . . ?
C17 C12 C11 121.35(13) . . ?
C12 C13 C14 120.44(15) . . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 119.8 . . ?
C15 C14 C13 120.66(15) . . ?
C15 C14 H14A 119.7 . . ?
C13 C14 H14A 119.7 . . ?
C16 C15 C14 119.22(15) . . ?
C16 C15 H15A 120.4 . . ?
C14 C15 H15A 120.4 . . ?
C15 C16 C17 120.40(15) . . ?
C15 C16 H16A 119.8 . . ?
C17 C16 H16A 119.8 . . ?
C16 C17 C12 120.57(15) . . ?
C16 C17 H17A 119.7 . . ?
C12 C17 H17A 119.7 . . ?
C19 C18 C4 132.25(14) . . ?
C19 C18 H18A 113.9 . . ?
C4 C18 H18A 113.9 . . ?
C18 C19 C21 125.31(15) . . ?
C18 C19 C20 119.39(14) . . ?
C21 C19 C20 115.28(14) . . ?
O2 C20 C19 125.88(16) . . ?
O2 C20 H20A 117.1 . . ?
C19 C20 H20A 117.1 . . ?
N2 C21 C19 177.09(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C1 C2 -178.27(13) . . . . ?
C9 N1 C1 C2 5.1(2) . . . . ?
C7 N1 C1 C6 1.4(2) . . . . ?
C9 N1 C1 C6 -175.24(13) . . . . ?
N1 C1 C2 C3 -177.81(13) . . . . ?
C6 C1 C2 C3 2.5(2) . . . . ?
C11 O1 C3 C2 2.7(2) . . . . ?
C11 O1 C3 C4 -177.34(12) . . . . ?
C1 C2 C3 O1 178.43(13) . . . . ?
C1 C2 C3 C4 -1.5(2) . . . . ?
O1 C3 C4 C5 179.74(12) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
O1 C3 C4 C18 0.36(19) . . . . ?
C2 C3 C4 C18 -179.67(14) . . . . ?
C18 C4 C5 C6 -179.59(14) . . . . ?
C3 C4 C5 C6 1.1(2) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
N1 C1 C6 C5 178.55(14) . . . . ?
C2 C1 C6 C5 -1.8(2) . . . . ?
C1 N1 C7 C8 -85.87(18) . . . . ?
C9 N1 C7 C8 90.96(17) . . . . ?
C1 N1 C9 C10 -87.29(17) . . . . ?
C7 N1 C9 C10 95.90(16) . . . . ?
C3 O1 C11 C12 -178.03(12) . . . . ?
O1 C11 C12 C13 -140.73(13) . . . . ?
O1 C11 C12 C17 40.48(18) . . . . ?
C17 C12 C13 C14 -0.2(2) . . . . ?
C11 C12 C13 C14 -178.98(14) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C14 C15 C16 C17 0.4(2) . . . . ?
C15 C16 C17 C12 -0.6(2) . . . . ?
C13 C12 C17 C16 0.4(2) . . . . ?
C11 C12 C17 C16 179.25(14) . . . . ?
C5 C4 C18 C19 4.0(3) . . . . ?
C3 C4 C18 C19 -176.69(15) . . . . ?
C4 C18 C19 C21 1.8(3) . . . . ?
C4 C18 C19 C20 -179.76(15) . . . . ?
C18 C19 C20 O2 -176.65(16) . . . . ?
C21 C19 C20 O2 1.9(2) . . . . ?
C18 C19 C21 N2 -180(100) . . . . ?
C20 C19 C21 N2 2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.042